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Dysifragilones A–C, Unusual Sesquiterpene Aminoquinones and Inhibitors of NO Production from the South China Sea Sponge Dysidea fragilis
Author(s) -
Jiao WeiHua,
Xu TingTing,
Zhao Feng,
Gao Hao,
Shi GuoHua,
Wang Jie,
Hong LiLi,
Yu HaoBing,
Li YuShan,
Yang Fan,
Lin HouWen
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403487
Subject(s) - sesquiterpene , chemistry , sponge , stereochemistry , circular dichroism , nitric oxide , inhibitory postsynaptic potential , absolute configuration , lipopolysaccharide , carbon skeleton , organic chemistry , botany , biology , neuroscience , endocrinology
Dysifragilones A–C ( 1 – 3 ), three unusual sesquiterpene aminoquinones based on a rearranged avarone skeleton, were isolated from the South China Sea sponge Dysidea fragilis . Their structures were elucidated by detailed spectroscopic and spectrometric analysis, and their absolute configurations were assigned from calculated electronic circular dichroism (ECD) spectra. The inhibitory activity of each compound on the production of nitric oxide (NO) stimulated by lipopolysaccharide (LPS) in mouse RAW 264.7 macrophages was evaluated. Of the three metabolites, dysifragilone A ( 1 ) showed the most potent inhibitory activity, with an IC 50 value of 6.61 ± 0.54 μ M .